


Unusual Punishment

by AgentK



Series: Finding A Place For Himself [1]
Category: Original Work
Genre: Double Penetration, Dungeons & Dragons, FTM, FtM Transgender, Half-Elf, Half-orc, M/M, Mildly Dubious Consent, Spanking, Tiefling, Transgender
Language: English
Status: Completed
Published: 2018-05-26
Updated: 2018-05-26
Packaged: 2019-05-13 21:32:43
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,720
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14756697
Author URL: https://archiveofourown.org/users/AgentK/pseuds/AgentK
Summary: A young thief is given an unconventional punishment when he's discovered stealing in a rival gang's territory.





	Unusual Punishment

**Author's Note:**

> [[ Brief warning: this story features a trans man as the main character. At some points his genitals are referred to with terms that are generally more associated with "female" anatomy so I recommend to avoid if that makes you dysphoric! "Breasts," "clit," "slit" and "cunt" are the ones I used - I generally find these words have a more masculine sound than, say, "boobs" or "pussy" but I understand it's a personal choice. ]]

“Hey, boss. We caught the little bluejay.” 

Aldyn squirmed, a taller and stronger man holding each of his arms and dragging him through the door into the gang’s hideout. “Bluejay” was his code name in his own thieves’ gang. They’d been targeting a shop in the other gang’s territory tonight, and he’d been caught. 

Aldyn was a slight, pretty half-elf, twenty years old, not very tall, with tan skin and chin length shaggy bluish-purple hair (thus the nickname.) He was dressed in tailored black trousers, a crisp white dress shirt with a purple ribbon tie, and a quite fancy purple and silver coat with nice black leather boots. All stolen, of course. He narrowed his silver eyes upon seeing the boss of the competing thieves’ guild, a towering half-orc who was large even for his race and facing the smaller man with a predatory smirk. 

“Well, well. I’ve only ever seen you from a distance.” He approached Aldyn and stroked his face, leering. “You’re a pretty little thing.” Aldyn couldn’t help trembling a little, for fear of a severe beating or even dismemberment. Competition for territory was fierce, and he couldn’t expect the leader of a rival gang to be kind. 

“You’re so pretty, in fact, that I’m going to give you a choice. Usually I deal with meddling brats like you by beating them until they’re unconscious and then waking them up to take one of their fingers. But you’re so cute, and awfully young. So I’ll let you keep your fingers and restrict the beating to your little backside if you let me have you, right here, in front of my men.” He stroked Aldyn’s cheek again, then tugged his hair gently. “But you have to consent to it. It’s your choice.” 

Aldyn blushed hotly, but tried to puff himself up, responding haughtily. “Is that even a punishment? I _like_ being fucked and getting my ass beat.” He knew it might get him into trouble, but his pride wouldn’t allow him to consent meekly. 

The half-orc laughed. “I like you, kid. But trust me, you’ll be a snivelling, sobbing little wreck by the time I’m done with you.” He nodded at the men who had dragged him in, and they went to stand by the door. Next he started to remove Aldyn’s coat. “Skinny little brat. Don’t you steal any food?” 

“I eat plenty.” Aldyn flinched slightly as the larger man started to unbutton his shirt, revealing the garment he used to bind his breasts. His face flushed. 

“Oh? What’s this?” The half-orc unlaced the binder, tossing it aside. Aldyn squinted his eyes shut, his face burning as his small breasts were revealed. The gang boss ran a rough, calloused thumb over Aldyn’s left nipple, grinning. “Are you what I’m thinking you are, then? A very special sort of boy. Take off the rest of your clothes.” Still blushing, Aldyn kicked off his boots and slipped off his trousers, socks and underpants. He’d never been naked in front of so many people before. The gang boss leered at him. 

“Even better. You’re going to get fucked hard in both of your holes, little bluejay.” He smirked. “I bet you’re going to love it… at first, anyway. My name is Gaskus, by the way. In case you want to scream it later. But first, it’s time to punish you. You won’t want to sit down for a few days after this.” Aldyn cried out in surprise as the half-orc tossed him over one shoulder and carried him towards a shabby old desk in the corner. He dumped Aldyn unceremoniously face down on the desk, then picked up a thick cushion from the chair behind it. “Raise your hips, little bluejay. What’s your real name, anyway?” 

“A-Aldyn.” He was too taken aback by the question to consider lying. 

“Pretty name. Suits you.” He shoved the cushion under Aldyn’s hips, raising them, and roughly yanked his legs apart. “Ever been spanked, Aldyn?” 

“Sometimes. Not… like this.” 

Gaskus laughed. “No, I expect not.” A heavy hand crashed hard into Aldyn’s vulnerable bare backside. “You have a cute little round ass. Expected it to be flat since you’re so skinny.” He spread Aldyn’s cheeks and ran a fingertip across his anus, causing the boy to shudder. “Nice tight little hole too. I’m really going to enjoy you.” His hand continued to descend onto Aldyn’s rear, and Aldyn grit his teeth and tried not to react. But it was futile. The man was more than twice his size, and strong. His hand was like a paddle that conformed to the shape of Aldyn’s burning, aching bottom. It wasn’t long before tears were streaking his face and he hiccuped back sobs. 

“That’s right, sing for me, little bluejay.” He continued until Aldyn was sobbing helplessly, trying to keep his eyes closed so he wouldn’t have to see the six other men in the room watching him get spanked. His backside throbbed, but he was aware of another ache between his legs. He’d always enjoyed a little spanking before sex, and even though this was a more intense experience, the desire was still there. The smacking stopped, and Aldyn cried out in shock as two fingers were suddenly thrust inside him.

“Let’s see how you’re liking this… oh, you’re dripping wet. You naughty little brat.” The fingers were withdrawn, and Aldyn was roughly flipped onto his back, hips still elevated by the cushion underneath him. “Demerian, get over here. Hold his legs back for me.” A tall tiefling man strode over and casually pulled Aldyn’s legs back towards his chest, leaving his thighs spread lewdly, exposing his moist sex. Gaskus held his dripping fingers to Aldyn’s lips. “Clean me up, you little pervert.” Aldyn grimaced slightly but licked his fluids from the half-orc’s hand. Gaskus tousled his hair then, and reached down to stroke Aldyn between his legs again, palming over his sex instead of penetrating him, applying gentle pressure. Aldyn arched his back slightly with a whimper, pressing against the hand. He couldn’t help it. 

“Ever been spanked here?” Aldyn shook his head, looking slightly horrified. “I bet it’ll make you even wetter, you little slut.” He lifted his hand and smacked the aching area between Aldyn’s legs, right over the slit, continuing to spank him until the entire area was warm, reddened and slick and Aldyn was panting and whimpering, tears starting to streak his flushed face again. Two fingers were thrust inside him once more and his hips spasmed. “Whine all you want, but you’re loving it. Little whore.” The older man rubbed a thumb over Aldyn’s clit and he bit his lower lip with a shudder. “So wet. Ready for my cock now, aren’t you, you filthy little brat?” 

Aldyn nodded, eyes closed, trembling. The tiefling let go of his legs, and Gaskus pulled him to his feet, taking the cushion off the desk. He took his own trousers and underpants off and sat down on it, pulling Aldyn towards him. Aldyn swallowed hard, looking down at the biggest cock he’d ever seen. 

“Don’t worry, sweetheart, you’re wet enough to take it. Though you’ll certainly be sore tomorrow. Demerian, lift him up so he can put his legs around me.” Aldyn flinched as he was casually grabbed from behind and lifted into the air. “Put your legs around my waist, little bluejay. Sink down onto my cock, nice and slow.” Aldyn bit his lip as the half-orc’s massive member began to stretch him open, and the man holding him held him steady as he slid down, the huge shaft filling and stretching him. He wrapped his arms around Gaskus’ shoulders, gasping as he was impaled. “Impaled” was the only word to describe it - he was being penetrated more fully than he ever had been before. There was a bit of pain in his lower stomach, but also a yearning desperation to writhe against the invasion. The man holding him stepped back, now that Aldyn was clinging to Gaskus with his feet resting on the desk. 

Gaskus chuckled warmly, placing both hands on Aldyn’s aching backside. “You’re so wet. Tight, though. Don’t know why you bother being a thief, you’d be an asset to any whorehouse.” He squeezed Aldyn’s left nipple, and the younger man whimpered. “D-don’t want to do this every night. M-more fun to get good and pent up.” Gaskus laughed. “You’re a treasure, bluejay.” Holding onto Aldyn’s hips, he began to slide the smaller man up and down on his huge cock, moving Aldyn’s body instead of his own. Aldyn cried out, pained at first, but gradually getting used to the massive presence inside him. A knot of pleasure formed in his belly and he grew wetter and wetter, shuddering and whimpering as he was repeatedly thrust into. 

“Good boy. Good, pretty boy.” The gang boss stroked his hair as Aldyn squirmed and whined. Then the older man reached down between Aldyn’s buttocks and rubbed his anus, causing him to flinch and tighten around his cock. Gaskus laughed quietly. “Ready to have your little ass filled up too?” Aldyn blinked, startled. “A-at the same time?” 

“Sure. Never had that done before? God, you’re going to love it, I can tell. Little slut like you. Demerian, you want the honour?” 

“Fuck, yes. He’s adorable.” The tiefling came closer, and Aldyn heard the rustle of his clothes being removed. Soon something slick prodded at Aldyn’s rear entrance, and he flinched again. 

“Don’t worry. I’ve got some oil in here. It’d be a crime to damage a pretty little ass like that.” Aldyn bit his lip again as a finger slid into his rectum, soon followed by another. He’d been fucked in the ass before, but never while being fucked in front as well. The feeling was not unpleasant, and he found his hips rocking back and forth, against the fingers and Gaskus’ cock in turn. Demerian leaned in close, speaking near his ear. “You like that, you slutty little brat?” 

“Y-yeah,” Aldyn panted wantonly, squirming. “Go on, stick it in me.” Demerian pulled his fingers out and gave Aldyn a stinging smack on the ass, laughing. “You’re fun.” Aldyn went still as the tiefling slowly sank his well-lubricated cock into his aching ass, flinching and spasming as he was filled from both sides. “F-fuck,” he whined, digging his fingers into Gaskus’ broad, muscular back. Demerian murmured against his neck. “You can say that again, little bluejay. Nine hells, you’re tight.” 

Aldyn kept his eyes closed and clung to Gaskus as Demerian began to thrust into his ass. The tiefling also reached up and cupped Aldyn’s breasts with both hands as he fucked him. Aldyn’s hips could no longer move much - he was simply held in place, impaled on Gaskus’ massive cock as Demerian, who was quite well-endowed himself, pounded him from behind, slamming his hips into Aldyn’s well-spanked backside. It was overwhelming, and he began to cry quietly, more out of desperation to reach orgasm than from pain. His genitals felt hot, throbbing, almost liquid. Gaskus stroked his hair soothingly. Demerian thrust faster and harder, and moments later Aldyn let out a choked sob as the tiefling came inside him, pinching his hardened nipples and biting his neck. Demerian withdrew his slick cock and smacked Aldyn’s throbbing rear. Gaskus placed his large hands on Aldyn’s bottom again, and once more started sliding him up and down on his huge dick. Aldyn could hear Demerian speak. “You’re a damned good fuck, little bluejay. You should see yourself, riding that cock, red ass spread open, cum dripping out of your stretched little hole.”

Aldyn moaned, clinging to Gaskus, face pressed against his massive shoulder. His insides fluttered and spasmed. Gaskus brought his hands to Aldyn’s back and spoke. “Lean back, little one. I’ve got you.” Aldyn leaned back and Gaskus supported him with one broad hand, reaching down with the other to rub his aching, swollen clit. He moved his thumb in circles over it and Aldyn whimpered helplessly, pressing his hips down as his sore, stretched cunt throbbed and clenched around the cock inside him. “F-fuck… FUCK!” The older man increased the pressure as Aldyn sobbed and trembled, legs tightening around Gaskus’ waist as he rapidly approached a gasping, shuddering orgasm. Aldyn dug his fingertips hard into Gaskus’ shoulders as he came, crying out in overwhelmed ecstasy. Gaskus gave him a moment to come down, then started sliding him up and down his cock again, faster than before, prompting further sobs and exhausted whimpers until finally he pulled Aldyn’s tired body down against his own, hard, clutching his sore buttocks in both hands as he came hard inside him, flooding him with semen that mixed with Aldyn’s own fluids, dripping down his cock and out of Aldyn’s aching hole. He held Aldyn close for a few moments, stroking his hair almost lovingly, murmuring quietly. “Good boy. Good, pretty little slut.” He beckoned the tiefling. “Come help him up, Demerian.” Aldyn was lifted up and set on his feet while Gaskus got up, then Demerian laid him down gently on top of the desk on his back. Too exhausted to be self-conscious, Aldyn sprawled out, legs slightly spread, both holes dilated and leaking. 

“Fuck, bluejay, you are quite a sight. I’ll be back with something to clean you up.” A moment later Gaskus brought Aldyn a damp washcloth and unceremoniously lifted his legs into the air, wiping his anus and genitals gently, finishing up with a little pat to the throbbing, swollen area between his legs. “Now, I’m not quite done with you, but I’ll try to make this quick. I was going to put you over a barrel and strap you until your ass blistered, but after that performance… let’s just say I’m a little reluctant to hurt you that much. You were one hell of a good fuck, and you’re very charming. But you still need to be taught a lesson, so I’m going to put you over my knee and paddle your cute backside good and hard. Then you can go home… though I expect you’ll be doing so very slowly and carefully. Okay?” 

Aldyn looked up, exhausted, and managed a weak nod. The thought of objecting crossed his mind, but he knew he was lucky to escape with no permanent wounds. 

Gaskus picked Aldyn up, tossing him over his shoulder again, and sat down in the chair behind the desk. As easily as if he were tossing a rag doll, he flipped the smaller man across his knee. Opening a desk drawer, he pulled out a sturdy, thick wooden paddle, which he rubbed across Aldyn’s already sore backside. He lifted it up and delivered a solid crack across both cheeks, and Aldyn flinched. “Are you going to try to rob a shop in our territory again, you slutty little brat?” 

“N-no, sir!” 

“Damned right.” Gaskus launched a flurry of quick, firm blows to Aldyn’s aching little backside, and it didn’t take long to bring the exhausted boy to tears. However, the half-orc implacably continued, the paddle landing on increasingly red and swollen, then bruised skin, until Aldyn had been sobbing wholeheartedly for a good five minutes. There was still a fair amount of cum inside him, which trickled out of both entrances and down his thighs as he was beaten. Finally the blows stopped and Gaskus spoke. “Good. By tomorrow, your cute little ass should be as blue and purple as your hair. You’ll have a reminder to behave yourself every time you sit down for at least a week.” Gaskus pulled Aldyn into a sitting position on his lap and wiped his tears from his face with his rough fingers, then picked up the damp towel to wipe between his legs again. “There, there, little bluejay. I’m not angry any longer. You were a lot of fun to play with. And if you ever want to play again, just come see me. I won’t tell anyone. If you’re a good boy we could skip the paddling, but you’d definitely be spanked in any case. And I’m sure you’ll need at least a week to recover.” 

Aldyn managed a weak, shaky smile as he replied, his entire body exhausted and aching, tears still streaming down his flushed face. “A-at least.”


End file.
